Where to Stay:

Ben and I stayed at Summercamp Hotel and honestly I can’t imagine there is anywhere more perfect to stay on the island. It was cost effective but truly lovely, centrally located, and so accommodating. We had free coffee at a station right outside our room and they gave us free bikes that we used to explore the island, something that would have cost us over $70 each to rent every day! I’m only giving one recommendation here because I haven’t found a single other place on the island I would compare to Summercamp. ​

2. How to Travel

The island includes six towns. I’ve divided my recommendations between those towns. Summercamp is located in the town of Oak Bluffs and we used the public bus system to travel between towns. Because we went in May, the island wasn’t at all crowded, yet but it was warm enough to walk if the bus stop was a little far from our destination. We only had to call an Uber once to get to a beachside dinner destination and otherwise, we used all-day public bus passes that were just $8 each!​

3. Where to Eat

Breakfast:

Oak Bluffs: Back Door Donuts - These are island famous and the apple fritters sell out fast! Get here early!Vineyard Haven: Waterside Market - Ben got a DELICIOUS breakfast burrito here and I got a hot caramel latte that was perfectly made. The vibe in this one makes it a can’t-miss stop. Aquinnah: Orange Peel Bakery - Getting here was one heck of a commitment. The closest bus stop was about 2 miles away so we literally hiked through the woods to get to this isolated forest bakery that is just a dream. We had a chocolate chip cookie and blueberry lemon cake that were both well worth the hike. Lunch:

Edgartown: Sea Shanty - With a view of the harbor and a breezy open patio, this is a no brainer for lunch. We ordered and split the BBQ pork flatbread and basically gorged on the free popcorn. Aquinnah: Helman’s Cafe - This little cafe is located in the middle of a tiny neighborhood way off the beaten path. Everything on the menu is truly farm-to-table and the avocado toast was just perfection. Menemsha: Larsen’s Fish Market - Located just off Gay Head Cliffs, this seafood shack prepares their famous lobster rolls, bisque, and chowder from just caught lobster. This makes you feel like the truest local.

Dinner

Edgartown: The Dunes - This high end restaurant won for us as our one expensive dinner stop and it was one hundred percent worth it. We had grilled swordfish, sweet pea risotto, and grilled asparagus and goodness, it was worth every penny. Oak Bluffs: Giordano's - This is a great stop to pick up a picnic dinner for the beach or on your hotel balcony. Grab a slice of pizza and a side of pasta with garlic bread. We also swung by the convenience store for a bottle of wine and had the perfect picnic dinner. Coffee & SnacksOak Bluffs: Black Dog Cafe - Located right next to the Harbor, this is the perfect spot for pour over and a treat from the bakery as you walk the path around the harbor. Edgartown: Mad Martha’s Ice Cream - Well. Ben called the Reese’s ice cream from Mad Martha’s the very best ice cream he has ever had. He may or may not have eaten a cone two times a day everyday we were there….Edgartown: Behind the Bookshelf - There is almost nothing I love more that having a cup of coffee created by someone who is just deeply passionate about the process. I had a muddled iced mint latte (the best latte I’ve ever had, and this is a big deal) and a lavender latte. DO NOT SKIP THIS. Drinks

​Oak Bluffs: Offshore Tavern - The best fries of my life right here. I mean if Ben was here he would tell you they have great craft beer. But the most important part is that the lemon rosemary fries will blow your mind. Oak Bluffs: Nancy’s - Also located on the Oak Bluffs harbor, this is a great stop for nighttime drinks. Edgartown: Bad Martha’s - Bad Martha's is one of only two breweries on the island and Ben called the Vineyard Ale one of the best beers he has ever had. Check out the tasting room outside of Edgartown. Edgartown: 19 Raw Bar - Check out this spot right next to the bus stop to try the third island made beer from Washashore Brewing Company.

4. Where to Shop

Each of the towns has its own unique flair. For example, Edgartown is so quintessentially New England, with all the nautical decor, hydrangea bushes, and high end shops, while Oak Bluffs feel like an easy breezy island town with boardwalk shops and tons of grab and go options. Here are some unique and gorgeous shops that you shouldn’t miss. Edgartown: This town is THE MOST DARLING PLACE IN THE WORLD. For real. Do not miss the ORIGINAL Vineyard Vines, Lilly Pulitzer, Edgartown Books, and Rose Water Market. Oak Bluffs: Grab a super discounted sweatshirt or t-shirt by ducking into all the (almost identical) shops that you see on boardwalks everywhere and haggling for a good price. Also check out Black Dog General Store!​

5. What to Do

Oak Bluffs: Ride bikes to East Chop Lighthouse and take a stroll among the historic Gingerbread Houses and Temple. Edgartown: Hike to Edgartown Lighthouse and South Beach for some of the loveliest views on the island. Menemsha: Visit the Martha's Vineyard Cultural Center, Gay Head Cliffs, and still functioning Gay Head Lighthouse.